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The Role of the C-3 Substituent in the Asymmetric Dihydroxylation of Hexo-5-Enofuranosides |
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| Authors: | Hari Babu Mereyala P Mallikarjun Goud Rajendrakumar Reddy Gadikota Rama Krishna Maddala K Ramasubba Reddy |
| Abstract: | ABSTRACT Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α® and β® is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α® exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5. |
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